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WO1999012923A1 - Composes indoliques stereo-isomeres, leur procede de preparation et leur utilisation - Google Patents

Composes indoliques stereo-isomeres, leur procede de preparation et leur utilisation Download PDF

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Publication number
WO1999012923A1
WO1999012923A1 PCT/JP1998/003727 JP9803727W WO9912923A1 WO 1999012923 A1 WO1999012923 A1 WO 1999012923A1 JP 9803727 W JP9803727 W JP 9803727W WO 9912923 A1 WO9912923 A1 WO 9912923A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
alkyl group
aralkyl
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1998/003727
Other languages
English (en)
Japanese (ja)
Inventor
Masao Mori
Masako Nakagawa
Atsushi Nishida
Mihoko Fuwa
Haruo Saito
Takayuki Matsunaga
Satoshi Takahashi
Chika Hasegawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lead Chemical Co Ltd
Original Assignee
Lead Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP9241417A external-priority patent/JPH1180154A/ja
Priority claimed from JP2697998A external-priority patent/JPH11228573A/ja
Priority to HK01101323.5A priority Critical patent/HK1030419B/xx
Application filed by Lead Chemical Co Ltd filed Critical Lead Chemical Co Ltd
Priority to KR1020007002384A priority patent/KR100572483B1/ko
Priority to EP98938943A priority patent/EP1020465B1/fr
Priority to DE69839056T priority patent/DE69839056T2/de
Priority to AU87493/98A priority patent/AU746588B2/en
Priority to CA002302402A priority patent/CA2302402C/fr
Priority to US09/486,318 priority patent/US6348484B1/en
Publication of WO1999012923A1 publication Critical patent/WO1999012923A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • R represents a hydrogen atom, an alkyl group, an aralkyl group, a cycloalkyl group, an aryl group, a monovalent metal atom, an amine or an ammonium: * indicates the position of an asymmetric carbon atom. ⁇ .
  • the present invention also provides the following formula (2)
  • the amino-stereoisomeric indole compound represented by the above formula (la) is obtained by converting the tributane represented by the above formula (2) to the following formula (3a)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Nouveaux composés indoliques stéréo-isomères, représentés par la formule générale (1), dans laquelle Y est (2) ou (3), (* représentant la position d'un atome de carbone asymétrique), [où X est alkyle C1-C5 éventuellement substitué par OH, carboxyle, amino, méthylthio, mercapto, guanidyle, imidazolyle ou benzyle; et R1 et R2 sont indépendamment H, alkyle, aralkyle, cycloalkyle ou aryle]; et R est H, alkyle, aralkyle, cycloalkyle, aryle, un métal monovalent, amine ou ammonium). Pour préparer ces composés, on condense le tryptophane avec un acide α-amino ou un acide carboxylique stéréo-isomère, de façon à former un amide; puis en soumet l'amide à une cyclisation oxydative, de façon à former directement un noyau oxazole. Ces composés ayant une activité physiologique, telle que l'inhibition de la peroxydation lipidique, ils peuvent être utilisés comme inhibiteurs de la peroxydation lipidique, dans lesquels ils représentent les principes actifs.
PCT/JP1998/003727 1997-09-05 1998-08-24 Composes indoliques stereo-isomeres, leur procede de preparation et leur utilisation Ceased WO1999012923A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US09/486,318 US6348484B1 (en) 1997-09-05 1998-08-24 Stereoisomeric indole compounds, process for the preparation of the same, and use thereof
CA002302402A CA2302402C (fr) 1997-09-05 1998-08-24 Composes indoliques stereo-isomeres, leur procede de preparation et leur utilisation
HK01101323.5A HK1030419B (en) 1997-09-05 1998-08-24 Stereoisomeric indole compounds, process for the preparation of the same, and use thereof
KR1020007002384A KR100572483B1 (ko) 1997-09-05 1998-08-24 입체이성 인돌 화합물, 그 제조방법 및 용도
EP98938943A EP1020465B1 (fr) 1997-09-05 1998-08-24 Composes indoliques stereo-isomeres, leur procede de preparation et leur utilisation
DE69839056T DE69839056T2 (de) 1997-09-05 1998-08-24 Stereoisomere indolderivate, verfahren zu ihrer herstellung und ihre verwendung
AU87493/98A AU746588B2 (en) 1997-09-05 1998-08-24 Stereoisomeric indole compounds, process for the preparation of the same, and use thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP9241417A JPH1180154A (ja) 1997-09-05 1997-09-05 立体異性インドール化合物、その製造方法および用途
JP9/241417 1997-09-05
JP10/26979 1998-02-09
JP2697998A JPH11228573A (ja) 1998-02-09 1998-02-09 インドール化合物、その製造方法および用途

Publications (1)

Publication Number Publication Date
WO1999012923A1 true WO1999012923A1 (fr) 1999-03-18

Family

ID=26364843

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1998/003727 Ceased WO1999012923A1 (fr) 1997-09-05 1998-08-24 Composes indoliques stereo-isomeres, leur procede de preparation et leur utilisation

Country Status (10)

Country Link
US (1) US6348484B1 (fr)
EP (1) EP1020465B1 (fr)
KR (1) KR100572483B1 (fr)
CN (1) CN1188409C (fr)
AT (1) ATE384717T1 (fr)
AU (1) AU746588B2 (fr)
CA (1) CA2302402C (fr)
DE (1) DE69839056T2 (fr)
RU (1) RU2182908C2 (fr)
WO (1) WO1999012923A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001012626A1 (fr) * 1999-08-13 2001-02-22 Lead Chemical Co., Ltd Composes d'indole, procede de preparation et utilisations de ces derniers
WO2004021984A3 (fr) * 2002-09-04 2004-11-25 Bristol Myers Squibb Co Composes aromatiques heterocycliques utiles en tant que secretagogues d'hormone de croissance
JP2010280712A (ja) * 2004-02-04 2010-12-16 Api Corporation 光学活性を有するアルコール及びカルボン酸の製造方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201119651A (en) * 2009-10-26 2011-06-16 Lg Life Sciences Ltd Pharmaceutical composition comprising indole compound
KR101510936B1 (ko) * 2013-01-29 2015-04-10 제주대학교 산학협력단 비바리 비단망사 추출물을 유효성분으로 포함하는 자가면역질환 또는 염증질환의 예방 및 치료용 조성물
CN104650056B (zh) * 2013-11-21 2017-09-05 华中师范大学 一种5‑(3‑吲哚基)‑噁唑类化合物的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0038298B1 (fr) * 1980-04-10 1984-07-25 Sandoz Ag Isoxazolylindol-amines
JP3354258B2 (ja) * 1993-12-03 2002-12-09 富山化学工業株式会社 新規なインドール類またはその塩

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ABSTRACTS OF PAPERS. THE ANNUAL MEETING OF PHARMACEUTICAL SOCIETY OF JAPAN, XX, XX, vol. 116, no. 02, 1 January 1996 (1996-01-01), XX, pages 215, XP002917624 *
NISHIDA A., ET AL.: "FIRST TOTAL SYNTHESIS OF MARTEFRAGIN A, A POTENT INHIBITOR OF LIPIDPEROXIDATION ISOLATED FROM SEA ALGA.", TETRAHEDRON LETTERS, PERGAMON, GB, vol. 39., no. 33., 13 August 1998 (1998-08-13), GB, pages 5983 - 5986., XP002917626, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)01228-3 *
TAKAHASHI S, ET AL.: "STUDIES ON BIOACTIVE SUBSTANCES IN NATURAL RESOURCES (PART VI) ISOLATION AND STRUCTURE ELUCIDATION OF MARTEFRAGIN A", TOYAMA-KEN YAKUJI KENKYUJO NENPO - ANNUAL REPORT OF TOYAMAPREFECTURAL INSTITUTE FOR PHARMACEUTICAL RESEARCH, TOYAMA-KEN YAKUJI KENKYUJO, TOYAMA, JP, vol. 24, 1 September 1997 (1997-09-01), JP, pages 53 - 57, XP002917625, ISSN: 1340-8011 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001012626A1 (fr) * 1999-08-13 2001-02-22 Lead Chemical Co., Ltd Composes d'indole, procede de preparation et utilisations de ces derniers
WO2004021984A3 (fr) * 2002-09-04 2004-11-25 Bristol Myers Squibb Co Composes aromatiques heterocycliques utiles en tant que secretagogues d'hormone de croissance
US7166596B2 (en) 2002-09-04 2007-01-23 Bristol-Myers Squibb Co. Heterocyclic aromatic compounds useful as growth hormone secretagogues
US7589102B2 (en) 2002-09-04 2009-09-15 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
US7592354B2 (en) 2002-09-04 2009-09-22 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
US7799801B2 (en) 2002-09-04 2010-09-21 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
US7910601B2 (en) 2002-09-04 2011-03-22 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
US7977353B2 (en) 2002-09-04 2011-07-12 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
US8232291B2 (en) 2002-09-04 2012-07-31 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
US8557841B2 (en) 2002-09-04 2013-10-15 Bristol-Myers Squibb Company Heterocyclic aromatic compounds useful as growth hormone secretagogues
JP2010280712A (ja) * 2004-02-04 2010-12-16 Api Corporation 光学活性を有するアルコール及びカルボン酸の製造方法

Also Published As

Publication number Publication date
DE69839056T2 (de) 2009-01-15
AU746588B2 (en) 2002-05-02
AU8749398A (en) 1999-03-29
US6348484B1 (en) 2002-02-19
CA2302402C (fr) 2008-12-02
CN1269798A (zh) 2000-10-11
KR100572483B1 (ko) 2006-04-19
EP1020465B1 (fr) 2008-01-23
ATE384717T1 (de) 2008-02-15
HK1030419A1 (en) 2001-05-04
DE69839056D1 (de) 2008-03-13
KR20010023730A (ko) 2001-03-26
CA2302402A1 (fr) 1999-03-18
RU2182908C2 (ru) 2002-05-27
CN1188409C (zh) 2005-02-09
EP1020465A4 (fr) 2004-09-15
EP1020465A1 (fr) 2000-07-19

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